Al Capone Shines My Shoes

Moose has taken great risks to secure a place for his sister Natalie at the Esther P. Marinoff School, yet he dislikes visiting her there. Examine his complex feelings about the school and his reasons for sending her there.

Moose looks forward to visits from his school friend Scout, but his visits are never entirely enjoyable for Moose. In what ways does Scout create problems for Moose, and cause friction between Moose’s Alcatraz friends?

Discuss the role of sibling rivalry in Al Capone Shines My Shoes, especially the feelings of Piper and Theresa toward their baby brothers. Is there evidence that Moose himself feels jealous of his sister?

Moose’s attraction to Piper Williams becomes the subject of gossip at Building 64, which embarrasses him. What aspects of hers particularly attract him? Equally, what doesn’t he like about her, and why?

Piper seems starstruck by the mobster Al Capone, Alcatraz’s most infamous “guest.” Discuss some possible reasons for her fascination. In what ways does her behavior seem to mirror Capone’s own?

At their first meeting, Al Capone refers to Moose as “son.” What similarities, if any, do you see between Moose and the gangster? How are they different?

Moose, Natalie, and their friends combine their special talents to thwart the attempted jailbreak by Buddy Boy, Willy One Arm, and Seven Fingers. Discuss the kids’ abilities and how they used them in the rescue, while also considering how the three convicts’ own talents aided them in their plot.

Jimmy tells Moose that “this island is too small for pretending” (254). What does he mean by this, and how does it relate to Moose’s quarrels with his friends in the novel?